Hostname: page-component-8448b6f56d-mp689 Total loading time: 0 Render date: 2024-04-25T01:36:10.314Z Has data issue: false hasContentIssue false
  • English
  • Français

Versatile Syntheses of Various Homo- and Copolymers of Poly(1,4-Arylene Vinylene)S

Published online by Cambridge University Press:  21 March 2011

R. E. Martin ,
B. S. Chuah ,
R. H. Riehn ,
F. Geneste ,
F. Cacialli ,
R. H. Friend ,
A. B. Holmes  and
J. Morgado
R. E. Martin
Affiliation:
Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Pembroke Street, Cambridge, CB2 3RA, U.K
B. S. Chuah
Affiliation:
Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Pembroke Street, Cambridge, CB2 3RA, U.K
R. H. Riehn
Affiliation:
Cavendish Laboratory, Department of Physics, University of Cambridge, Madingley Road, Cambridge, CB3 0HE, U.K
F. Geneste
Affiliation:
Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Pembroke Street, Cambridge, CB2 3RA, U.K
F. Cacialli
Affiliation:
Cavendish Laboratory, Department of Physics, University of Cambridge, Madingley Road, Cambridge, CB3 0HE, U.K
R. H. Friend
Affiliation:
Cavendish Laboratory, Department of Physics, University of Cambridge, Madingley Road, Cambridge, CB3 0HE, U.K
A. B. Holmes
Affiliation:
Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Pembroke Street, Cambridge, CB2 3RA, U.K
J. Morgado
Affiliation:
Cavendish Laboratory, Department of Physics, University of Cambridge, Madingley Road, Cambridge, CB3 0HE, U.K
Get access

Abstract

The synthesis of poly(1,4-phenylene vinylene)s (PPVs) containing a 2,3-dialkoxy substitution pattern has been developed. Poly[2,3-bis(2-ethylhexyloxy)-1,4-phenylene vinylene)] (BEH-PPV, 4) was prepared and its optical properties compared with the recently discussed poly(2,3-dibutoxy-1,4-phenylene vinylene) (DB-PPV, 1), which showed in contrast to classical 2,5-substituted PPV derivatives a notable blue-shift of the longest-wavelength absorption (λmax) and a considerable increase of the solid-state photoluminescence (PL) efficiency. The two statistical PPV copolymers 5 and 6 comprising 2,3-dibutoxy and dimethyloctylsilyl- or 2,5-bis(dimethyloctylsilyl) side-chains, respectively, were synthesized via the Gilch dehydrohalogenation route. Double-layer light-emitting devices (LEDs) were demonstrated to combine high electroluminescence efficiencies with low turn-on voltages.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 598: Symposium BB – Electrical, Optical, & Magenetic Properties...V , 1999 , BB2.1
Copyright
Copyright © Materials Research Society 1999

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

1. Kraft, A., Grimsdale, A. C., and Holmes, A. B., Angew. Chem. Int. Ed. 37, 402 (1998).Google Scholar
2. Friend, R. H., Gymer, R. W., Holmes, A. B., Burroughes, J. H., Marks, R. N., Taliani, C., Bradley, D. D. C., Santos, D. A. dos, Brédas, J. L., Lögdlund, M., and Salaneck, W. R., Nature 397, 121 (1999).Google Scholar
3. Cacialli, F., Curr. Opin. Coll. Int. Sci. 4, 159 (1999).Google Scholar
4. Segura, J. L., Acta Polym. 49, 319 (1998).Google Scholar
5. Sheats, J. R., Chang, Y. L., Roitman, D. B., and Stocking, A., Acc. Chem. Res. 32, 193 (1999).Google Scholar
6. Burn, P. L., Kraft, A., Baigent, D. R., Bradley, D. D. C., Brown, A. R., Friend, R. H., Gymer, R. W., Holmes, A. B., and Jackson, R. W., J. Am. Chem. Soc. 115, 10117 (1993).Google Scholar
7. Spreitzer, H., Becker, H., Kluge, E., Kreuder, W., Schenk, H., Demandt, R., and Schoo, H., Adv. Mater. 10, 1340 (1998).Google Scholar
8. Chuah, B. S., Cacialli, F., Davies, J. E., Feeder, N., Friend, R. H., Holmes, A. B., Marseglia, E. A., Moratti, S. C., Brédas, J.-L., and Santos, D. A. dos, Mat. Res. Soc. Symp. Proc. 488, 87 (1998).Google Scholar
9. Cacialli, F., Chuah, B. S., Kim, J. S., Santos, D. A. dos, Friend, R. H., Moratti, S. C., Holmes, A. B., and Brédas, J.-L., Synth. Met. 102, 924 (1999).Google Scholar
10. Braun, D. and Heeger, A. J., Appl. Phys. Lett. 58, 1982 (1991).Google Scholar
11. Greenham, N. C., Samuel, I. D. W., Hayes, G. R., Philips, R. T., Kessener, Y. A. R. R., Moratti, S. C., Holmes, A. B., and Friend, R. H., Chem. Phys. Lett. 241, 89 (1995).Google Scholar
12. Hwang, D.-H., Kim, S. T., Shim, H.-K., Holmes, A. B., Moratti, S. C., and Friend, R. H., Chem. Commun., 2241 (1996).Google Scholar
13. Kim, S. T., Hwang, D.-H., Li, X. C., Grüner, J., Friend, R. H., Holmes, A. B., and Shim, H.-K., Adv. Mater. 8, 979 (1996).Google Scholar
14. Chu, H.-Y., Hwang, D.-H., Do, L.-M., Jang, J.-H., Shim, H.-K., Holmes, A. B., and Zyung, T., Synth. Met. 101, 216 (1999).Google Scholar
15. Helgeson, R. C., Tarnowski, T. L., Timko, J. M., and Cram, D. J., J. Am. Chem. Soc. 99, 6411 (1977).Google Scholar
16. Fields, D. L., Miller, J. B., and Reynolds, D. D., J. Org. Chem. 29, 2640 (1964).Google Scholar
17. Hawker, C. J. and Fréchet, J. M. J., J. Chem. Soc., Chem. Commun., 1010 (1990).Google Scholar
18. Hawker, C. J. and Fréchet, J. M. J., J. Am. Chem. Soc. 112, 7638 (1990).Google Scholar
19. Pommerehne, J., Vestweber, H., Guss, W., Mahrt, R. F., Bässler, H., Porsch, M., and Daub, J., Adv. Mater. 7, 551 (1995).Google Scholar